SYNTHESIS OF THE POTASSIUM-SALT OF 2,3,4,5-TETRAHYDRODIPICOLINIC ACID, A KEY INTERMEDIATE IN THE DIAMINOPIMELATE PATHWAY TO L-LYSINE

被引：15

作者：

COUPER, L

ROBINS, DJ

CHRYSTAL, EJT

机构：

[1] UNIV GLASGOW,DEPT CHEM,GLASGOW G12 8QQ,SCOTLAND

[2] ICI PLC,AGROCHEM,JEALOTTS HILL RES STN,BRACKNELL RG12 6EY,BERKS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期

关键词：

2,3,4,5-TETRAHYDRODIPICOLINIC ACID; DIAMINOPIMELATE PATHWAY; L-LYSINE BIOSYNTHESIS; ENZYME SUBSTRATE; IMINE FORMATION;

D O I：

10.1016/S0040-4039(00)79065-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The potassium salt (13) of 2,3,4,5-tetrahydrodipicolinic acid, a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7), has been prepared by elimination of p-toluenesulphinic acid from the N-toluenesulphonyl derivative (12) of dimethyl cis-piperidine-2,6-dicarboxylate with simultaneous cleavage of the ester groups. 2,3,4,5-Tetrahydrodipicolinic acid exists in solution in equilibrium with the corresponding enamine (15) and an open chain form (14), and serves as a substrate for meso-DAP dehydrogenase on the biosynthetic pathway to L-lysine (7).

引用

页码：2717 / 2720

页数：4

共 14 条

[1]

BHATTACHARJEE JK, 1983, AMINO ACID BIOSYNTHE, P229

[2] PROXIMITY EFFECTS .7. STEREOSPECIFIC SYNTHESES OF CIS-1,5-CYCLOOCTANEDIOLS AND TRANS-1,5-CYCLOOCTANEDIOLS [J].